I woke up at the Harmony House in Hazard, an eclectic B&B popular with passing travelers. Owned by Sherry and David, the old Victorian had been a music school in its past life in the ‘30s. Sherry had fully decorated it in classical music theme, with instruments all around the house and room names after famous composers - I stayed in Vivaldi room. Shortly after arriving, I would run into David, telling him about my day, and proceeded to get ready for my evening of delivery from KFC and drifting off into the night. I had a decent night’s sleep, a kind of deep sleep you experience knowing you were safe and comforted. I woke up early and had plans to hit the pavement by 7:30am. The Harmony House by 6am, was filling up with the scent of fresh breakfast, and I was eager to satisfy my other senses with it. David had been downstairs cooking up a comprehensive breakfast of eggs, hashbrowns, toast, bacon and fruit with a pot of delicious coffee to round things out. After hearing my story the evening before, he decided to surprise me with a present and arm me with dog pepper spray for the continuation of my Kentucky journey.

We ended up eating breakfast together, as Sherry was not feeling too well. David was an environmental scientist for the State of Kentucky. His primary job was working with coal industry as a biologist. Sherry was also a small business owner, and the B&B was something they always wanted to have as a joint project to meet and support travelers when they were not busy with their respective careers. They were fascinated by the people they would meet and stories they would hear. David and I dove into many topics from education, the state of Kentucky and its politics – a dangerous grounds for a San Franciscan snowflake such as myself to walk on. We surprisingly were very aligned on many issues. His passion being a Kentuckian through-on-through was around job reskilling for the community to pivot away from fossil fuel as well as lift a large demographic out of poverty. This was an area I was also very deeply passionate about, and had started a program at Oracle prior to leaving, to see how a technology provider can partner with local governments in aiding that job reskilling from an industry perspective. It is a win-win for all parties involved; it just needs focus and commitment.

But the more interesting conversation was about relationships. After four decades together with Sherry, I asked him what was the secret to their longevity? He said they gave each other space to do things that made them happy, as long as their relationship would not suffer because of them. He said he was always supportive of Sherry’s passion in so many areas, and her happiness ultimately led to their happiness. It is amazing the two meaningful encounters I had so far were similar in nature. These were true partnerships with dedication, admiration and support between two strong people.

Now armed with delicious calories, a very visible and accessible knife, pepper spray and energy from a delightful conversation, I started my day in a content state, but ready to take on any challenges that would come my way. I was feeling good for the first 5 miles, but that feeling would be short lived as I would enter a familiar place, with my intuition causing a heightened awareness very quickly. My legs, and mace in one hand locked and loaded, I would not be ambushed today. If things were going to go down, I was going to inflict damage back. Now, for you animal lovers, before you start criticizing me, I would encourage you to be surrounded by 8 dogs while trying to get away on a 12% incline, finally giving up and getting off the bike that remains the only thing between you and your fate. My mind was not thinking about speaking to the owners about responsible dog ownership at that moment. It’s said that reasoning is a luxury as long as life is reasonable. And these were not reasonable situations to encounter.

That said, my first responders were always going to be my legs followed by mace. But if I was going to get off my bike this time, while the enemy continued to advance, then there was certainly going to be blood shed – most likely from both. I was prepared for an all-out battle... And my fears were realized when dogs slowly started coming out to the side of the road as the sound of my bicycle approaching notified them to get into position. Imagine staring at your future, because that is what I was looking at. These were not small dogs, ranging from a German Shepherd to a Pit Bull and a very angry looking mix. But, I had to keep progressing and would do so with trepidation. And then, an unexpected ally in the form of a truck appeared out of nowhere, descending upon the battle ground as in a scene from an epic World War II cinematic masterpiece, aptly titled “Saving not-so-private Tazbaz.” The truck having a full visibility into the situation, started getting in between the dogs and me, pushing them back into their dog space and preventing them from launching attacks. With now reinforcement at my side, I picked up the pace to get through the stretch. The truck amazingly stayed with me for about 3 miles until I cleared enemy lines. I was elated and waved with tremendous gratitude when they would eventually leave me knowing I would be ok.

After this incident, the day became fun, and I started to just play! My favorite activity became the “stare offs” I would have with dogs, during times I had the upper hand of barreling down a hill at 40 miles an hour. Our eyes locked in as I would oh so slightly point my bike towards their direction; I can see it in their defeated look, a moment of reckoning when they’re faced against an unstable man. They would kindly wave me by without the need to exercise any dog masculinity and we would learn to co-exist for that moment.

The day was about obstacle courses, entering some of the more heavily damaged areas due to the floods. I had to cross two collapsed bridges, one by carrying my bike down and up the debris, and the other by backtracking to find a pathway on to the train tracks that ran adjacent to the road. To me, this was part of the experience, and I was just enjoying it – not the destruction, but the challenge as a smile became permanently fixed on my face throughout the day.

As I made my way to western Kentucky, the dark, lonely and sometime heavy feelings the environment would impose on me began dramatically shifting with a terrain that was open, bright and had a sense of happiness to it. There was a Grand Canyonesque rock formation of brilliant red and orange hues nestled amongst stunning greens of the forest it partnered with. I would pass Buckhorn, one of the destinations I had to alter; spend a night in McKee, giving me a sense normalcy as I cooked dinner at my Airbnb; then be charmed by the town of Berea with its beautiful brick buildings, manicured lawns and charming town center. Berea was another stop I had to change and was looking forward to staying at the historical Boone Tavern – I would like to go back.

Making my way out of Berea onto my next destination of Harrodsburg, I would notice even more drastic changes to the environment I was playing in. Kentucky was becoming flatter, and three things started to happen: the famous head winds I had read about from the east to west travelers started saying hello; I begin to drift into my thoughts I had not visited since the start; and I began to sing a different tune about not wanting to sing a tune so I can be one with the road. The Best of Eagles might be in future on the roads of Kansas.

But Kentucky still had a bit of mischievous, a sense of playfulness left with it. Just as I assumed that I had reached the end of hilly terrain, Kentucky had more beauty it wanted to present me with. I started meandering around the snugly tucked in roads surrounded amongst dense beautiful trees. When I would get used to that, it would spit me out in to lush green rolling hills along beautiful country homes. And when I would get comfortable with where I was, it would present me with a climb up slightly high enough above the groves that would lay beneath my feet as plush carpet. It also showed its sense of humor with playing practical jokes like making me go up a 19% grade hill with tired legs that comes with at the end of a ride. I was falling in love with Kentucky after a very rocky start to our relationship. Even the first adversity to our day was avoided when a kind soul created a sanctuary for cyclist by providing a rest stop and bottled waters for refill.

Getting closer to my destination for the evening, I would hear the distant rumblings of thunder, now knowing I would end the near perfect day under heavy rain. It is amazing how quickly nature can turn on you, but I did not care. It was all valid; all part of why I was here.

The next two days would present me with the opportunity to decompress and enjoy the gentle rolling hills, making my way to the second rest day stop in Falls of Rough before concluding my time with Kentucky. I went through the farmlands and home of Maker’s Mark, as my environment became more and more predictable. When life is predictable the benefit is that you relax, take in deep, purposeful breaths. But was this who I really was deep down inside? It was the first time asking this question to myself, thinking about the dichotomous sides of me of being a tech executive with the life that comes with it vs. desiring for what I was experiencing at this very moment.

I had gain an hour from crossing my first time zone towards where the day would end, but it would be too early to arrive. I decided to just sit under a tree on a hilltop side, staring at the prairie ahead as the beautiful melodies of Melody Gardot filled my air.

“If the world was mine, I’d paint it gold and green

I’d make the oceans orange for a brilliant color scheme

I would color all of the mountains, make the sky forever blue

So the world would be a painting and I’d live inside with you.”

I had one more day of riding left in Kentucky before crossing into Illinois, but I knew deep down inside this was the moment and feeling I wanted to remember it by. And with that, I said goodbye to Kentucky and the wonderful Kentuckians.

-Troy